
Vacation rentals with a kayak in McHenry County
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Top-rated kayak rentals in McHenry County
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House rentals with a kayak

Lakefront Paradise
The place was quiet and comfortable, perfect for getting some rest. I would recommend it to anyone looking for a relaxing stay.

Walk 2 lake, HOT TUB, pool table, bikes & kayaks
We had amazing girls getaway weekend here. Short walk to Lake Como and short drive to Lake Geneva. Between the hot tub, the fire pit, the karaoke, it had everything you needed to stay in and was close enough to Lake Geneva if you wanted to go out. Highly recommended!

Lakefront, beautiful views, spacious and private.
I'm extremely grateful for this beautiful home. We woke up to swans and all forms of life greeting us in the morning. incredible spot!

Entertain on The Chain! water sports and sauna.
Tucked along the quiet northern edge of Antioch, this house doesn’t just offer a place to stay - it gives you something to feel. Vaulted ceilings, custom barnwood beds, and raw concrete countertops set the tone: warm, solid, and built with intent. The private beach isn’t flashy - it’s better. Soft sand, still water, and no reason to rush. Grill outside, gather at the big family-style table, then sweat it all out in the sauna that feels like it was made to erase stress. The beds hit the sweet spot between firm and forgiving. Every corner of the place feels curated without being pretentious. Jewel is just up the road if you need supplies, but you’ll quickly forget the outside world exists. And Waylon? The kind of host you rarely get - quick to respond, genuinely helpful, and fully dialed in without hovering. This isn’t just a weekend rental - it’s the kind of place that makes you rethink how you spend your time off. You’ll leave better than you arrived.

Corner Lakefront Property
Perfect place to stay for my son's graduation from the Navy Academy. Very flexible to the fact we extended our stay to spend more time with our Sailor.. Felt Right At Home!!! Thank you Jacqueline & Mark.. ;-)

Riverfront rental with fun activity
Ur home was beautiful n relax to stay there n fun to be in the lake love it thank u luci for letting us stay at ur beautiful home

Beautiful Lakehouse sleeps 12 Boat/Pets/HotTub/Ski
Great host. Really looked after us and communicated very well.

Our Sweet Retreat is waiting for you
This home was very cute and very comfortable. The beds and linens were very comfortable. The home is well stocked with everything you need. The neighborhood is super peaceful. Lake is just down the street with 2 small park areas with swings/play equipment for the kids. There are also 3 restaurants along the lake with one in walking distance. Downtown Lake Geneva is minutes away. We had a very nice and peaceful time.
Cottage rentals with a kayak

Cozy Cottage-blocks from lake-garage arcade room
The house was perfect! Last minute some friends and I decided to do a quick getaway while on spring break and Toninas house was more than exceptional! The garage was so cool with all the games and sitting area, the house is easily walkable from the lake, and Tonina responded to me with great suggestions on where to eat and other activities to do for our specific age group (21-25) and some other family friendly suggestions. She is a great host and has a lot of knowledge of the area! We’re already talking about plans to book for the summer when the lake is open!

Twin Lakes Bungalow
Fantastic stay—very clean and completely stocked. We had a blast as did our dog! Would definitely recommend!

The Lily Pad at Lake Wandawega
This stay is amazing for quiet mornings with coffee on the deck. It’s right on the water with the ability to kayak and paddle board. The amenities are amazing and it’s the perfect place for a couples getaway weekend. Close distance for day trips to Lake Geneva or concerts at Alpine Valley!

Connie's Cottage on the Lake.
Connie’s house is a beautiful find on a small lake in southern Wisconsin. If you’re looking for a retreat from city life, this is the place. The home is comfortable and cozy with a great patio and a great game room. We really enjoyed the fussbal. We were there in the winter, but I’m sure the lake provides plenty of activities in the summer. Overall, a great option under 2 hours from the city. Recommended!

Cozy 2 bedroom cottage on lake Delavan with kayaks
Tiffany was extremely accommodating and responsive with every question my wife and I had. The location was beautiful, quiet and there was lots of activities to do in the surrounding areas. The lake house itself was clean and had everything you could need for a weekend stay!

Lakefront Cottage w/Boat Rentals
GREAT place. Gorgeous. Excellent restaurants in walking distance. Clean space. Only issue for us was the beds were _far_ too soft and pillowy for us, but that's a personal preference.

Lakefront cottage with gorgeous sunset views
We just spent 4 nights at this location. We were in the area to celebrate the holidays with our kids and grandkids. Since it was winter and there was snow on the ground, we didn't use a lot of the outdoor amenities, but we could tell it would be amazing when the weather was nice. The house was perfect for our needs. It had nice sized rooms, two updated bathrooms, nicely equipped kitchen, a great view of the lake, and really good internet. I had a couple of questions when we arrived and Jenn responded very quickly. We will definitely consider staying there again when we are in the area for a multiple day stay.
Cabin rentals with a kayak

Go Camp Como! Walk to Lake Geneva's Como Lake!
Wonderful stay! Put children and grands loved this place! Our 3 adult children and spouses together with our 5.8 grandchildren had a marvelous time! They all Live in Chicago so camp comp Was a breath of fresh air- stomping around in the backyard creek, playing both inside and out with the hidden forts , outdoors and indoors fires and the little play house was darling ! The kids had such a wonderful time on the outdoors egg hunt for Easter ! Thanks sooo much! We may return!!!

Hunter Cabin on Petite Lake, Ol Pine Lodge Cabins
Will definitely be recommending to any family or friends that want a waterfront getaway! Robyn and Tim were fantastic hosts and welcoming from the very second we stepped out of the car. The location of the property makes you feel secluded but also part of the lake life experience of the "Chain" all at the same time. Friends nearby had no trouble picking us up from the private pier for a boat ride, and Robyn also offered up use of the kayaks right away. The only thing I would change was how much time we were able to stay at the cabins and utilize the fire pit/beach/deck/etc. Need a stay in the future!

Enjoy a Getaway @ The Lake-Heim by Chain-O-Lakes
Hosts were very nice, they did a special thing for Valentine’s Day that I asked for (actually, they did more then I was expecting!). Communication was very good and they were very attentive to everything. I love it and I’m definitely going back on summer!

Spacious 2BR Cabin@The Lake-Heim
The place is amazing. It was just what we needed for a weekend getaway. Looking forward to coming back next time.

Living the Lakehouse Dream
Really enjoyed staying here. The host was incredibly responsive, and the place is a perfect getaway

ELK Cabin on Petite Lake, Ol Pine Lodge Cabins
Tim & Robin's place was wonderful! The cottage (#1) was exactly like the pictures and was very clean. Tim & Robin live on-site and we were greeted upon arrival. Through the weekend we had several passing conversations that were very pleasant. They had lots of solid recommendations and made sure we were comfortable. The property itself was simply dreamy! There was a nice beach area as well as an elevated deck overlooking the lake. We would definitely recommend renting here and plan on returning at some point in the future.

Large Lake Cabin – EV Charger, Peloton, Ski Nearby
We enjoyed our stay here very much. The place was nicely decorated and the views were wonderful. Amenities such as kayaking and canoeing, for lake activities were great as well. Marina was very responsive and accommodating. We also lost our phone by the dock and needed extra time to find it. She was very understanding and accommodating. We loved the outside dining area as well as indoors one and bonfire outside area was wonderful. The only minor complaint was that the bunk beds were not as comfy. But overall we loved it here and would definitely recommend this place and host again. Main room takes the cake for the most amazing window view of the lake. ;) It’s also very close to Lake Geneva and all the wonderful places there. Browne lake is also very lovely too. Definitely plan your next getaway here. ;) Thank you for having us. ;)
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- Wilmot Mountain Ski Resort
- Six Flags Great America
- 875 North Michigan Avenue
- Lincoln Park Zoo
- Grand Geneva Resort & Spa
- Wicker Park
- Chicago History Museum
- Willis Tower
- Alpine Valley Resort
- Brookfield Zoo
- Racine North Beach
- Lincoln Park
- Geneva National Resort & Club
- Illinois Beach State Park
- Richard Bong State Recreation Area
- Skokie Country Club
- Garfield Park Conservatory
- Chicago Cultural Center